Editor's note: Gloria Borger is a senior political analyst for CNN, appearing regularly on CNN's "The Situation Room," "AC360°" and "State of the Union," as well as participating in special event coverage.

(CNN) -- The thing that is hard to miss in Ted Olson's Washington office are the quills. They're in a mug, all 56 of them, each commemorating an appearance before the Supreme Court. In many of those cases, he was the standard bearer for conservatives. And a successful one; he won 44 times.

In fact, one of his most satisfying and famous wins was against Al Gore, the Democrats and super-attorney David Boies in the contested 2000 election. Olson represented George W. Bush.

The rest, as they say, is history. Olson won, Boies lost. That is except in the movie "Recount," as they both joked to me. Boies won the docudrama.

On Wednesday, the two men won, this time together.

They teamed up to argue against Proposition 8, which bans gay marriage in California. The legal team won in a stunning and clear decision.

The plaintiffs, U.S. District Judge Vaughn Walker wrote, "demonstrated by overwhelming evidence that Proposition 8 violates their due process and equal protection rights," ruling it unconstitutional.

Now, the case will work its way up to the 9th Circuit Court of Appeals, and then to the high court. Only Olson and Boies will be on the same side this time.

In this case, Olson has been at the center in so many ways. Disdained by many conservatives for arguing for gay marriage, some openly calling his decision as an act of pure ego or even treason.

Indeed, conservative legal analyst Ed Whelan told me, "It really is a betrayal of everything Ted Olson has purported to stand for in his legal career in terms of constitutional principles."

But if you listen to Olson, his constitutional principles are exactly what this case -- and his decision to take it on -- is all about.

"The Constitution trumps everything," he told me. "The Constitution provides that equal protection of the laws shall be guaranteed to all citizens."

Never mind that more than 40 states have voted against gay marriage or that a majority of the American public doesn't support it. That was the case, he says, with a ban on interracial marriage struck down by the U.S. Supreme Court more than 40 years ago.

"Civil rights battles are won by fighting for civil rights. ... We're representing real people, who are being deprived of their constitutional rights, and we tell them to wait? For what? For how long?"

It's interesting, in a way, because opposition to gay marriage increasingly looks like it cuts along a generational divide.

One recent study showed that 58 percent of Americans ages 18 to 29 support gay marriage, while only 22 percent of those 65 and older feel the same way. So if the issue will gradually resolve itself, some say, why take it to court now?

"Our choice is yes we will go to court to fight for you because your constitutional rights are being ignored. ..." Olson told me. "Or we could tell [gay couples] why don't you wait for years, why don't you wait for another generation?"

Even some pro-gay marriage groups were skeptical at first, worried that Olson and Boies were setting the cause up for failure. Still other legal scholars say that the two super-lawyers are driven by ego and relish that one last shot at arguing an historic case before the court. Both men cringe at that.

And what about the charge that the two lawyers figure they can game the high court -- even a conservative one?

Ah, says Olson. "We're not taking for granted any votes on the Supreme Court. We have so much respect for the judges that are hearing this case and the justices of the Supreme Court that will hear this case, none of whom have made up their minds."

Is he sure? "Yes," he smiles. "They have not heard the arguments."

Now they almost certainly will. And Olson will get his 57th quill.

The opinions expressed in this commentary are solely those of Gloria Borger.